The 11 best things to do in Outer Cape this weekend

October 30–November 1, 2026 · handpicked from everything on across Outer Cape.

Spooky Bear weekend in Provincetown dominates the calendar, with drag brunches, cabaret, and live music, while Orleans and Wellfleet bring live music, Halloween parades, and family fun. Plan around a few Provincetown headliners and spread the rest across the Outer Cape towns.

WITCH PERFECT – Oct. 30th ShowFriday · 7:00 PM · ProvincetownWitch Perfect is an all live-singing comedy parody of Hocus Pocus featuring Emmy-winning stars from RuPaul's Drag Race All-Stars, with doors at 6:30 and the show at 7 on Friday.SIRENS: Live Music – Spooky BearFriday · 7:00 PM · ProvincetownSIRENS at the Crown & Anchor is a sapphic-themed night of live music and fierce vocals, a good fit for a Friday out during Spooky Bear.SIRENSFriday · 3:00 PM · ProvincetownA night of live music from local Provincetown singers Marissa, Darlene and Lily Mae, a relaxed way to start the weekend in town.Power Load AC/DC Cover BandFriday · 2:00 PM · Hog Island Beer Co. · OrleansPowerload brings a night of AC/DC favorites to Hog Island Beer Co. in Orleans on Friday, with food available and a good crowd of rock fans to join.Drag BrunchSaturday · 11:00 AM · Post Office Cafe & Cabaret · ProvincetownProvincetown's Post Office Café & Cabaret hosts a high-energy drag brunch on Saturday where local drag performers take the stage.Dark Rooms:Jackie CoxSaturday · 7:00 PM · Red Room · ProvincetownJackie Cox returns to the Red Room with DARKROOMS, an adults-only cabaret billed as her filthiest yet, for a late Saturday show.The Fine CorinthiansSaturday · 8:30 PM · OrleansThe Fine Corinthians play The Barley Neck in Orleans with a blend of styles, led by pianist and composer Bill Pernice, a quiet listening option on Saturday night.Halloween Parade and Monster BashSaturday · 1:00 PM · Wellfleet Cultural District · WellfleetWellfleet's free Halloween Parade starts at 1 PM at Town Hall and ends with a party at Baker's Field, with free refreshments, a great family outing.SOLID GOLD TEA - Spooky Bear WkndSunday · 4:00 PM · Boatslip Resort & Beach Club · ProvincetownSolid Gold Tea at Boatslip brings 70s and 80s disco hits remixed by DJ Maryalice on Sunday, with dress-up encouraged for a Studio 54 feel.Pumpkin Palooza!Saturday · 6:00 PM · Wellfleet Preservation Hall · WellfleetPumpkin Palooza at Wellfleet Preservation Hall runs 6 to 8 PM on Halloween with outdoor games, a pumpkin maze, a dance party, and free candy, all free to attend.TRYSTER ACT: BRUNCH OF THE DEAD 1PM – Spooky BearSunday · 1:00 PM · Crown & Anchor · ProvincetownTryster Act's Brunch of the Dead at Crown & Anchor is a Sunday drag brunch with a sinful twist, a relaxed way to close out the weekend in Provincetown.

Looking for the current weekend? See what’s on in Outer Cape this weekend →